scholarly journals Tandem Triphosgene-Assisted Metal-Free One-pot Preparation of Nitriles and Amides from Aldehydes and Ketones

2021 ◽  
Author(s):  
Jianguo liu ◽  
Xiu-Zhi Wei ◽  
Longlong Ma
Keyword(s):  
Metal Catalysts ◽  
Organic Base ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Aldehydes And Ketones ◽  
Ester Linkage ◽  
Hydrolysis Of ◽  
By Products

Here we report a facile and efficient triphosgene-assisted one-pot conversion of aldehydes/ketones into nitriles/amides. The triphosgene, a kind of phosgene alternative, containing both ester linkage and chloromethyl units, easily reacts with oximes for the preparation of nitriles/amides. However, the reaction of oximes with triphosgene can’t fully convert corresponding nitriles/amides due to hydrolysis of oximes to aldehydes or ketones. Our protocol tandem proceeds smoothly without the use of organic base and metal catalysts. Diverse functionalized aromatic, aliphatic, and allylic aldehydes/ketones incorporating biomass-derived platform compounds were successfully converted to nitriles and amides in excellent yields. Compared to step-by-step reaction, this tandem strategy is characterized by multi-step reaction in one pot, mild reaction conditions, and fewer by-products.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

Dry ice-mediated rational synthesis of edge-carboxylated crumpled graphene nanosheets for selective and prompt hydrolysis of cellulose and eucalyptus lignocellulose under ambient reaction conditions

2020 ◽  
Vol 22 (16) ◽  
pp. 5437-5446 ◽  
Author(s):  
Hassan Idris Abdu ◽  
Kamel Eid ◽  
Aboubakr M. Abdullah ◽  
Mostafa H. Sliem ◽  
Ahmed Elzatahry ◽  
...  
Keyword(s):  
Graphene Nanosheets ◽  
Ambient Conditions ◽  
Selective Hydrolysis ◽  
Reaction Conditions ◽  
One Pot ◽  
Dry Ice ◽  
Hydrolysis Of Cellulose ◽  
Hydrolysis Of ◽  
Crumpled Graphene

Edge-carboxylated graphene (ECG) crumpled nanosheets with tuneable COOH content were synthesized by a facile one pot approach for selective hydrolysis of cellulose to glucose and eucalyptus to xylose and glucose under ambient conditions.

scholarly journals Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2525-2538 ◽  
Author(s):  
James Bull ◽  
Renzo Luisi ◽  
Leonardo Degennaro
Keyword(s):  
Transition Metal ◽  
Physicochemical Properties ◽  
Direct Synthesis ◽  
Transition Metal Catalysts ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
New Procedures

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

scholarly journals One-Pot, Metal-Free Synthesis of Dimethyl Carbonate from CO2 at Room Temperature

2020 ◽  
Vol 1 (3) ◽  
pp. 298-314
Author(s):  
Santosh Govind Khokarale ◽  
Thai Q. Bui ◽  
Jyri-Pekka Mikkola
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Dimethyl Carbonate ◽  
High Selectivity ◽  
Chemical Species ◽  
Side Reactions ◽  
Ambient Conditions ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free

Herein, we report on the metal-free, one-pot synthesis of industrially important dimethyl carbonate (DMC) from molecular CO2 under ambient conditions. In this process, initially the CO2 was chemisorbed through the formation of a switchable ionic liquid (SIL), [DBUH] [CH3CO3], by the interaction of CO2 with an equivalent mixture of organic superbase 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and methanol. The obtained SIL further reacted with methyl iodide (CH3I) to form DMC. The synthesis was carried out in both dimethyl sulfoxide (DMSO) and methanol. Methanol is preferred, as it not only served as a reagent and solvent in CO2 capture and DMC synthesis, but it also assisted in controlling the side reactions between chemical species such as CH3I and [DBUH]+ cation and increased the yield of DMC. Hence, the use of methanol avoided the loss of captured CO2 and favored the formation of DMC with high selectivity. Under the applied reaction conditions, 89% of the captured CO2 was converted to DMC. DBU was obtained, achieving 86% recovery of its salts formed during the synthesis. Most importantly, in this report we describe a simple and renewable solvent-based process for a metal-free approach to DMC synthesis under industrially feasible reaction conditions.

Enhanced one-pot selective conversion of cellulose to ethylene glycol over NaZSM-5 supported metal catalysts

2021 ◽  
Author(s):  
Sreejith Sreekantan ◽  
Arun Arunima Kirali ◽  
Banu Marimuthu
Keyword(s):  
Ethylene Glycol ◽  
Sol Gel ◽  
Metal Catalysts ◽  
Supported Metal Catalysts ◽  
Reaction Conditions ◽  
One Pot ◽  
Cellulose Conversion ◽  
Moderate Reaction ◽  
Gel Method ◽  
Sol Gel Method

The mesopores/micropores NaZSM-5 was synthesised by sol–gel method. The 5%Al–8%Ni–25%W/NaZSM-5 catalyst exhibited the highest cellulose conversion of 100% with EG yield as high as 89% (C mol%) at moderate reaction conditions which is highly applicable in polymer Industry.

Metal free one-pot synthesis of α-ketoamides from terminal alkenes

RSC Advances ◽  
2015 ◽  
Vol 5 (58) ◽  
pp. 47265-47269 ◽  
Author(s):  
Sayan Dutta ◽  
Surya Srinivas Kotha ◽  
Govindasamy Sekar
Keyword(s):  
Practical Approach ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Terminal Alkenes

A practical approach towards the synthesis of α-ketoamides from terminal alkenes has been developed using I2/IBX under one-pot reaction conditions.

An Improved Synthesis of Urea Derivatives from N-Acylbenzotriazole via Curtius Rearrangement

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3443-3450 ◽  
Author(s):  
Anoop S. Singh ◽  
Anand K. Agrahari ◽  
Sumit K. Singh ◽  
Mangal S. Yadav ◽  
Vinod K. Tiwari
Keyword(s):  
Reaction Time ◽  
Column Chromatography ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Urea Derivatives ◽  
Curtius Rearrangement ◽  
Short Reaction Time ◽  
Metal Free ◽  
Salient Features

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N-acyl, and cyclic ureas in good yields from N-acylbenzotriazoles by treating the latter with various amines in the presence of TMSN3/Et3N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

scholarly journals Simple one-pot synthesis of thioureas from amine, carbon disulfide and oxidants in water

2016 ◽  
Vol 81 (3) ◽  
pp. 219-231 ◽  
Author(s):  
Milutin Milosavljevic ◽  
Ivan Vukicevic ◽  
Sasa Drmanic ◽  
Jasmina Nikolic ◽  
Aleksandar Marinkovic ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Carbon Disulfide ◽  
Reaction Times ◽  
Tetraacetic Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Industrial Level ◽  
By Products ◽  
Operational Simplicity

The present study reports the new facile methodology for synthesis of symmetrical and asymmetrical thioureas by an one-pot reaction of amine, carbon disulfide and oxidants: hydrogen peroxide, ethylenediamine tetraacetic acid (EDTA)/sodium percarbonate system or air. The structures of the synthesized compounds were confirmed by IR, 1H and 13C NMR and MS methods. Reaction mechanism has been proposed on the basis of reaction intermediate isolation and their structure determination. The synthetic benefits of the presented methods is reflected in the operational simplicity, mild reaction conditions, short reaction times, recycling of solvent, high purity and yield of products, absence of dangerous by-products and technological applicability at industrial scale. Considering commercial importance of the thioureas, it can be emphasized that implementation of the optimal synthesis of thiourea, based on presented methods, at industrial level of production would provide concurrent alternative to existing technologies in use.

A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives

2016 ◽  
Vol 69 (1) ◽  
pp. 98 ◽  
Author(s):  
Kang Lei ◽  
Dong-Wei Sun ◽  
Yuan-Yuan Tao ◽  
Xiao-Hua Xu
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Good Yield ◽  
Substitution Reaction ◽  
High Tolerance ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Intramolecular Nucleophilic Substitution

A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker–Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transition metal-free and mild reaction conditions, and high tolerance for functionality, thereby allowing easy substitutions around the frutinone A core.

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